Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 8: Q54b (page 262)

Question: Which of the following alcohols could notbe made selectively by hydroboration–oxidation of an alkene? Explain.

Short Answer

Expert verified

Answer

Possible

Step by step solution

01

Step 1: Anti-markovnikov’s rule

In hydroboration-oxidation reaction two steps occur:

  • Hydroboration- It occurs in an anti-Markovnikov manner, where hydrogen (from BH3) attaches to the more substituted carbon and BH2to less substituted carbon in double-bonded carbon. It is syn addition which means that the hydroboration takes place on the same face of the double bond.
  • Oxidation step involves the replacement of BH2 with hydroxyl group.
02

 Step 2: Alcohol possible or not:

Given alcohol is possible when a double bond is between C2and C3 as both are equally substituted so can attach to any side. Other alcohol possible is the same as given. Thus, this alcohol is made selectively.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

What products would you expect from oxymercuration-demercuration of the following alkenes?

a)

b)

Question: What product would you expect to obtain from addition of to 1,2-dimethyl-cyclohexene? Show the stereochemistry of the product.

What alkenes might be used to prepare the following alcohols by hydroboration-oxidation?

Dichlorocarbene can be generated by heating sodium trichloroacetate.

Propose a mechanism for the reaction, and use curved arrows to indicate

the movement of electrons in each step. What relationship does

your mechanism bear to the base-induced elimination of HCl from

chloroform?

The following alkene undergoes hydroboration–oxidation to yield a single product rather than a mixture. Explain the result, and draw the product showing its stereochemistry.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Organic Chemistry

Read Explanation

Chemical Reactions

Read Explanation

The Earths Atmosphere

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free